The Insert Files using Google Drive window appears. Select the files you want to attach.

At the bottom of the page, decide how you want to send the file:

Drive link works for any files stored in Drive, including files created using Google Docs, Sheets, Slides, or Forms. Attachment only works for files that weren’t created using Google Docs, Sheets, Slides, or Forms.

Click Insert.

Gmail will check to see if your recipients have access to the file. If they don’t, you’ll be prompted to change the sharing settings of the file before you send your message.

Microsoft had beaten Google to this feature with its OneDrive (earlier called SkyDrive) integration for Outlook 2016 and Outlook.com. OneDrive is seamlessly connected to Office apps and Office Online.

When you try to attach one or more files that are over 20 MB in size Outlook.com will prompt you to upload the files to your OneDrive account. The recipient will receive a link to the file instead of the file itself in their inbox.

The Microsoft account you use to sign in to Outlook.com automatically signs you into OneDrive as well. Upload your large file to your OneDrive account. To access your OneDrive, click the paperclip icon and select your file from the OneDrive location.

Store the attachment in Dropbox and use the Dropbox for Gmail Chrome extension to send and preview files and links without leaving your Gmail window. The extension adds a Dropbox icon to the compose window. Click the icon and select the file from your Dropbox contents. The attachment is actually a link and not a physical file included in the email.

As a recipient, you can rich previews of all Dropbox links shared in emails. Just like attachments, you can use these links to download the file directly from Gmail or add it to your Dropbox. If your file transfer fails, look through these bandwidth restrictions.

File Dropper isn’t integrated with any email program, but it allows you to upload files up to 5GB in size each. You don’t even have to create an account. Upload a single file or a set of files. You’ll receive a link to each file you upload and you can paste that link into an email to email the file to someone. Files will be deleted if they aren’t downloaded at least once every 30 days.

WeTransfer appeals with a well-designed interface. Opt for the free WeTransfer that allows you to send 2GB of files to up to 20 people without a signup if you feel like it. But, even with the free account, you can send files as many times as you want. Add the recipient’s email, your email, and a small message if you want to. Send the file as an email or a link.

The paid WeTransfer Plus ($12 monthly) comes with more benefits and a bigger transfer quota of 20GB. You can not only send bigger files but also set delete dates, and password protect all files.

TransferBigFiles offers a few more features, such as a Chrome extension (and some apps) that gives you a button in Gmail for easy file uploads. There are several flavors of the service. The free account is a bit limited but it offers secure transfers.

The paid plans give you a 20GB per file upload limit. And a host of other features. You can protect your downloads with a password, set a custom expiry date, or get notified when the files are downloaded. The service supports multiple files and more than one recipient per email.

You’ll need to sign up to use the advanced features – you can use Transfer Big Files without signing up, but files will expire in 5 days. If you don’t want to sign up, you’re better off using one of the above services.

DropSend allows you to quickly send files from its homepage without signing up. You can also open an account and choose the free or the paid plans. The free plan gives you max file size of 4GB and five sends per month. Its most unique features are its file transfer tools. The Microsoft Outlook plugin allows you to attach large files to your email via your DropSend account.

DropSend Direct apps for Mac and Windows are drag-and-drop uploaders for easy file sharing. You can use it with the online storage space the service offers with its paid plans. DropSend also offers mobile apps for Android and iOS that work as interfaces for the cloud storage account.

File transfers are protected with 256-bit AES encryption as standard across the service.

EmailLargeFile is another mixed bag of free and paid file transfer service. Just 200MB per file with the free plan doesn’t sound much but you can send ten files every day to maximum three recipients. Email confirmations alert you when the files are downloaded. Files are encrypted and kept online for at least 15 days.

Do You Manage Your Large Email Attachments?

It is always wise to rely on the specialized cloud storage and transfer tools. Also, do remember that an email travels across multiple servers on its way to the recipient. Your Gmail attachment can be rejected for your file attachment if it is sent to a non-Gmail user. Request the sender to give you a delivery confirmation for important email attachments.

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Mathias Conradt

February 12, 2018 at 12:38 pm

Problem with the file drop services mentioned above are that the files are hosted on some unknown server and the service provider has access to your files. The same goes for Dropbox, Google Drive, etc. If you want a secure and private solution, even free of any costs due to open-source, you can just install Nextcloud (open-source Dropbox alternative) on your own server or shared hosting account - it only requires a simple LAMP stack - and you can share large files easily. Even comes with a free Outlook plugin. https://nextcloud.com

For Android devices, you can use PlayBak. Its really easy to send videos of any size to anyone via GMail, Email, Text Message, Facebook, Twitter, etc. Your recipients don't need any special apps to watch your video in HD

i started using clickandsend.com. It allows you to send unlimited file size and has cool email tracking options such as remotely deleting an already sent email or if you forgot to attach a file you can attach it after the email was sent - pretty cool if you ask me!

Works fine for me, but I did have some problems as a result of previously using Google Cloud Connect, which was integrated with Microsoft Office. As a result, none of my Office files would sync, and I could not uninstall Google Cloud Connect. The solution? I re-installed Google Cloud Connect and then immediately uninstalled it. Now everything syncs perfectly. I love Gmail and Gdrive.